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H40009

Sigma-Aldrich

2-Hydroxy-2-methylbutyric acid

98%

Synonym(s):

α-Hydroxy-α-methylbutyric acid, (±)-α-Hydroxy-α-methylbutyric acid, (±)-2-Hydroxy-2-methylbutanoic acid, (±)-2-Hydroxy-2-methylbutyric acid, 2-Hydroxy-2-methylbutanoic acid, 2-Methyl-2-hydroxybutyric acid

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About This Item

Linear Formula:
C2H5C(CH3)(OH)CO2H
CAS Number:
3739-30-8
Molecular Weight:
118.13
EC Number:
223-120-7
MDL number:
MFCD00004476
UNSPSC Code:
12352100
PubChem Substance ID:
24895608
NACRES:
NA.22

assay

98%

mp

73-75 °C (lit.)

SMILES string

CCC(C)(O)C(O)=O

InChI

1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)

InChI key

MBIQENSCDNJOIY-UHFFFAOYSA-N

Application

2-Hydroxy-2-methylbutyric acid can be used as:
  • A complexing agent in a new electrolytic system, applicable in the isotachophoretic lanthanide separation.[1]
  • An aldehyde surrogate to prepare pyrrolo[1,2-a]quinoxaline derivatives by reacting with 2-(1H-pyrrol-1-yl)aniline.[2]
  • A starting material to synthesize Cr(V) reagent named sodium bis(2-hydroxy-2-methylbutyrato)oxochromate(V) (Aldrich cat. no. ALD00006) applicable in the total synthesis of (−)-taxuyunnanine D.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBH7663
STBF6118V
STBD8432V
STBC4067V
S41251

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α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo [1, 2-a] quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
Viji M, et al.
Royal Society of Chemistry Advances, 10(61), 37202-37208 (2020)
W Dekant et al.
Research report (Health Effects Institute), (102)(102), 29-71 (2001-08-16)
The biotransformation of methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and tert-amyl methyl ether (TAME) was studied in humans and in rats after inhalation of 4 and 40 ppm of MTBE, ETBE, and TAME, respectively, for 4 hours, and
Separation and analysis of lanthanides by isotachophoresis coupled with inductively coupled plasma mass spectrometry
Vio L, et al.
Talanta, 99, 586-593 (2012)
Two-phase synthesis of (−)-taxuyunnanine D
Wilde NC, et al.
Journal of the American Chemical Society, 136(13), 4909-4912 (2014)
A Amberg et al.
Toxicological sciences : an official journal of the Society of Toxicology, 55(2), 274-283 (2000-06-01)
tert-Amyl methyl ether (TAME) may be widely used as an additive to gasoline in the future. The presence of this ether in gasoline reduces the tail pipe emission of pollutants. Therefore, widespread human exposure to TAME may occur. To contribute
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